Proton Transfer in N-(2-Hydroxy-1-naphthylmethylene)-1-pyrenamine and N,N′-Bis(2-hydroxy-1-naphthylmethylene)-p-phenylenediamine Crystals

Two kinds of N-(2-hydroxy-1-naphthylmethylene)aniline-type compounds, N-(2-hydroxy-1-naphthylmethylene)-1-pyrenamine (NPY) and N,N′-bis(2-hydroxy-1-naphthylmethylene)-p-phenylenediamine (DNP), have heen prepared as members of the N-salicylideneaniline family and subjected to structural studies in the crystalline state. In NPY, the hydrogen in the intramolecular N···H–O hydrogen bond has been found to locate not only at the oxygen site, but also at the nitrogen site, even at 120 K. A similar hydrogen-bond structure has also been found for DNP. This is mainly due to the π-electron delocalization effect. The relative stabilization of the proton transferred form (NH-form) compared with ordianry N-salicylideneanilines has been clearly indicated by solid-state NMR measurements.

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